Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living spaces. At the heart of the home is a chef's kitchen featuring custom cabinetry, high-end appliances, and stylish finishes. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living. Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living spaces. At the heart of the home is a chef's kitchen featuring custom cabinetry, high-end appliances, and stylish finishes perfect for both everyday living and entertaining. The open-concept living and dining areas flow seamlessly, enhanced by updated systems and central air conditioning for year-round comfort. Upstairs, the primary suite provides a serene escape with a spa-like tile bath and soaking tub. Two additional guest bedrooms share a beautifully appointed full bath that also includes convenient laundry. Unique details like a compass rose stained glass window add a distinctive nautical touch. The finished lower level offers even more living space, including a large bedroom ideal for guests or extended family. Outdoors, a stunning mahogany deck overlooks the newly landscaped backyard, complete with an outdoor shower and perfect areas for entertaining. With close proximity to downtown Vineyard Haven and the beaches of Vineyard Sound, this exceptional home captures the essence of island living timeless, refined, and move-in ready.
$1,999,000
5 Pine Tree Lane, Vineyard Haven, MA 02568
4beds
2,730sqft
Single Family Residence
Built in 1927
7,840 Square Feet Lot
$1,911,100 Zestimate®
$732/sqft
$-- HOA
What's special
Stylish finishesOutdoor showerConvenient laundryNewly landscaped backyardStunning mahogany deckGenerous living spacesSpa-like tile bath
- 55 days
- 638
- 35
Zillow last checked:
Listing updated:
Listed by:
Alyssa M Halisky 508-525-2584,
Wallace & Co. Sotheby's International Realty
Source: CCIMLS,MLS#: 22603526
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air
Appliances
- Included: Dishwasher, Electric Range, Refrigerator, Range Hood, Washer, Electric, Tankless Water Heater
- Laundry: Electric Dryer
Features
- Recessed Lighting, Walk-In Closet(s)
- Flooring: Hardwood, Wood, Tile
- Basement: Finished
- Number of fireplaces: 1
Interior area
- Total structure area: 2,730
- Total interior livable area: 2,730 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Driveway, Gravel
- Has uncovered spaces: Yes
Features
- Stories: 3
- Patio & porch: Deck, Porch
- Exterior features: Outdoor Shower, Underground Sprinkler System
- Fencing: Partial
Lot
- Size: 7,840 Square Feet
- Features: Cleared, Level
Details
- Parcel number: TISB M:0004F B:00000 L:00001
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Roof: Asphalt
Condition
- Year built: 1927
Utilities & green energy
- Water: Public
Community & HOA
HOA
- Has HOA: No
Location
- Region: Tisbury
Financial & listing details
- Price per square foot: $732/sqft
- Tax assessed value: $1,336,000
- Annual tax amount: $9,913
- Date on market: 7/21/2026
- Cumulative days on market: 31 days
Estimated market value
$1,911,100
$1.82M - $2.01M
$7,683/mo
Price history
| Date | Event | Price |
|---|---|---|
| 9/11/2026 | Pending sale | $1,999,000$732/sqft |
Source: MLS PIN #73480830 Report a problem | ||
| 8/25/2026 | Contingent | $1,999,000$732/sqft |
Source: LINK #43291 Report a problem | ||
| 7/1/2026 | Listed for sale | $1,999,000$732/sqft |
Source: LINK #43291 Report a problem | ||
| 6/26/2026 | Pending sale | $1,999,000$732/sqft |
Source: MLS PIN #73516062 Report a problem | ||
| 6/11/2026 | Contingent | $1,999,000$732/sqft |
Source: LINK #43291 Report a problem | ||
| 2/27/2026 | Price change | $1,999,0000%$732/sqft |
Source: MLS PIN #73480830 Report a problem | ||
| 10/1/2025 | Price change | $1,999,999+0%$733/sqft |
Source: MLS PIN #73410635 Report a problem | ||
| 9/18/2025 | Price change | $1,999,000-8.9%$732/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 7/15/2025 | Price change | $2,195,000-8.4%$804/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 5/17/2025 | Listed for sale | $2,395,000-3.8%$877/sqft |
Source: LINK #43291 Report a problem | ||
| 1/31/2025 | Listing removed | $2,490,000$912/sqft |
Source: LINK #42345 Report a problem | ||
| 9/2/2024 | Price change | $2,490,000-3.9%$912/sqft |
Source: Martha's Vineyard MLS #32400203 Report a problem | ||
| 7/31/2024 | Listed for sale | $2,590,000$949/sqft |
Source: LINK #42345 Report a problem | ||
| 7/19/2024 | Listing removed | $2,590,000$949/sqft |
Source: LINK #42204 Report a problem | ||
| 6/24/2024 | Listed for sale | $2,590,000+146.7%$949/sqft |
Source: LINK #42204 Report a problem | ||
| 4/28/2023 | Sold | $1,050,000-4.5%$385/sqft |
Source: LINK #40535 Report a problem | ||
| 3/10/2023 | Pending sale | $1,100,000$403/sqft |
Source: LINK #40535 Report a problem | ||
| 3/2/2023 | Listed for sale | $1,100,000+2100%$403/sqft |
Source: LINK #40535 Report a problem | ||
| 6/3/1998 | Sold | $50,000$18/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,896 -12.7% | $1,043,100 -8% |
| 2024 | $9,044 +7.2% | $1,133,300 -1.6% |
| 2023 | $8,435 +27.1% | $1,152,300 +51% |
| 2022 | $6,638 +2.6% | $762,943 +8.2% |
| 2021 | $6,468 +5% | $705,300 +6.8% |
| 2020 | $6,160 +1.8% | $660,215 +0% |
| 2019 | $6,054 +5.8% | $660,200 +9% |
| 2018 | $5,723 -0.2% | $605,600 -3.8% |
| 2017 | $5,737 +12% | $629,700 +12.6% |
| 2016 | $5,124 +11.1% | $559,400 +8.2% |
| 2015 | $4,610 -4.3% | $516,800 -10% |
| 2014 | $4,818 -0.9% | $574,300 +0.1% |
| 2013 | $4,863 -0.3% | $573,500 -5.8% |
| 2012 | $4,878 +2.2% | $609,000 -4.1% |
| 2011 | $4,774 +9.4% | $634,900 -4.4% |
| 2010 | $4,364 +7% | $664,300 -2.6% |
| 2009 | $4,078 +1.8% | $681,900 -6.5% |
| 2008 | $4,004 +8% | $729,300 +10.7% |
| 2007 | $3,708 +7.7% | $658,600 -0.5% |
| 2006 | $3,442 +2% | $661,900 +15% |
| 2005 | $3,374 +18.2% | $575,700 +63.1% |
| 2004 | $2,855 +4.7% | $352,900 |
| 2003 | $2,728 +5.6% | $352,900 |
| 2002 | $2,583 +4% | $352,900 +89.9% |
| 2000 | $2,484 | $185,800 |
Find assessor info on the county website
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